Chester Holidays from £1,091

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Your Chester Holiday

The best way to experience this vibrant city is with a custom-made Chester holiday package. Stay in the neighbourhood of Essex Village, which is good for walking, hiking and views or choose someplace else — our packages are all about you. Essex Steam Train, Goodspeed Opera House and Essex Island Marina are just some of the many sights you'll want to check out during your trip to Chester. Check out Expedia's extensive range of travel options and begin planning your perfect holiday to Chester now.

Top Chester Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Motel 6 New Haven - Branford, CT
Landing Furnished Apartment Near Yale University

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)
Population
1,550
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Harveys Beach, Goodspeed Opera House and Devils Hopyard State Park

Top hotels in Chester

Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

3 out of 5
2049 Norwich Montville CT
Fully refundableReserve now, pay when you stay
The price is £85 per night from 5 Apr to 6 Apr
£85
5 Apr - 6 Apr
includes taxes & fees
9.2/10 Wonderful! (2,669 reviews)
Was great

Reviewed on 26 Mar 2026

Hyatt Place Uncasville - Casino Area
Mohegan Sun

Mohegan Sun

4.5 out of 5
1 Mohegan Sun Boulevard Montville CT
9.2/10 Wonderful! (2,047 reviews)
Its a great place . Nice room..staff if is very accommodating

Reviewed on 25 Mar 2026

Mohegan Sun
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St Branford CT
Fully refundable
The price is £58 per night from 31 Mar to 1 Apr
£58
31 Mar - 1 Apr
includes taxes & fees
7.2/10 Good! (1,000 reviews)
You get why you pay for. We just needed a cheap stay for one night. The toilet seat was loose and falling off. The hallway smells like straight up cigarette smoke, and floors were a bit dirty. Pillows were super small (one per head basically). We didnt use the shower but I did look inside and the ...

Reviewed on 23 Mar 2026

Motel 6 New Haven - Branford, CT
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.